Recent years have witnessed extensive theoretical2 and ex-perimental3 interest in the small propellanes.4 Because of our previous involvement in the area31 and our extensive interest in derivatives of bicyclo[ 1.1.0] butane,5 we were intrigued with the possibility of studying the synthesis and reactions of the [n.l.l]propellanes. Shortly after the initiation of our studies in this area, reports of the synthesis of complex derivatives of the [4.1.1] propellane system appeared.6 Quite recently, the conversion of 1 into 2 has been reported.7 It was this report which prompted us to disclose our results on the synthesis and reactions of the parent hydrocarbon, [3.1.1]propellane (3).

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Upon irradiation in 2-propanol, A1-9-octahydroquinoline (1) gives trans-decahydroquinoline, 2-methyl-A1-piperideine (2) gives 2-methylpiperidine, AMsopropylidenepropylamine (7) gives Ar-propyl-2-aminopropane, and 2phenyl-A+pyrroline (8) gives 2,2,-diphenyl-2,2'-bipyrrolidine (9). Comparative photolyses of 2 and 7 and 8 and A-benzylidenecyclohexylamine (10) show that cyclic imines 2 and 8 do not show enhanced reactivity toward photochemical hydrogen abstraction reactions when compared with acyclic analogs. It is concluded that the low reactivity of the carbon-nitrogen double bond toward photochemical hydrogen abstraction reactions is not due only to rapid radiationless decay by twisting about the carbon-nitrogen bond.

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Der Isophthalsäurediester (I) wird katalytisch zu dem Cyclohexandiester (II) hydriert, aus dem durch Behandlung mit LiN(iPr)2 und anschließend mit MeI das Iodmethyl‐Derivat (III) entsteht.